This invention relates to novel organophosphorus amines, and more particularly relates to novel amine salts of 1, 4, 2-oxazaphospholidine-4-acetic acid, 2-alkoxy-2-oxides and the use of such compounds as a herbicide and plant growth regulator.
There are numerous references in the prior art that disclose various organophosphorus compounds. For example, U.S. Pat. No. 3,172,903 discloses that certain 1,3,2-oxazaphospholidine and 1,3,2-oxazaphospholidine phosphorus ester compounds are useful as fungicides. U.S. Pat. No. 4,190,651 discloses that certain 4-substituted 1,3,2-oxazaphospholidine derivatives are useful as insecticides. U.S. Pat. No. 4,387,060 discloses a synergistic insecticidial composition containing 2-(thi)oxo-1,3,2-oxazaphospholane of defined formula.
Other organophosphorus compounds are known to have biological activity on plants. For example, U.S. Pat. No. 3,799,758 to Franz discloses that N-phosphonomethylglycine and its salts are useful as a broad spectrum herbicide and has a phytotoxic effect on most terrestrial and aquatic plants. U.S. Pat. No. 4,486,359 to Brendel et al discloses that N-phosphonomethylglycine can be prepared from glycine and paraformaldehyde to obtain an intermediate which is reacted with a dialkylphosphite to obtain an ester of the desired compound, which is then hydrolized. U.S. Pat. No. 4,062,669 to Franz disloses that N-organo-N-phosphonomethylglycine-N-oxides and derivatives thereof are useful in herbicidal compositions and methods, and that the compounds and the compositions containing them are useful as phytotoxicants and as plant growth regulants. U.S. Pat. No. 4,601,744 to Sikorski et al discloses that ester of N,N'-methylene-bis-[N-[-(diaryloxyphosphinyl)methyl]glycine]are useful as herbicides.
Despite these and other references in the prior art, there is now provided a novel 1, 4, 2-oxazaphospholidine compounds that have selective phytotoxic activity, i.e. they have a herbicidal effect upon certain plant species but do not have a phytotoxic effect on other plant species, and have a plant growth regulant activity, i.e. stunt or retard the growth rate of certain plants without phytotoxicity.